


Story Per a Life

by AnotherWorld3111



Series: Angels and Demons Verse [17]
Category: Supernatural
Genre: Alternate Universe - Assassins & Hitmen, Alternate Universe - Gangsters, Alternative Universe - FBI, Assassin Dean Winchester, BAMF Castiel (Supernatural), Barebacking, Bondage, Bottom Dean Winchester, Castiel is pansexual and you can fight me on it, Cock Rings, FBI Agent Castiel (Supernatural), Handcuffs, Humor, Just for this ig, M/M, Mob Boss Sam Winchester, Orgasm Delay/Denial, Pigeons, Revenge, Top Sam Winchester, Undercover Missions, Versatile Castiel
Language: English
Status: Completed
Published: 2019-11-26
Updated: 2019-11-26
Packaged: 2021-02-26 02:54:02
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 5,221
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/21576355
Author URL: https://archiveofourown.org/users/AnotherWorld3111/pseuds/AnotherWorld3111
Summary: Castiel's backstory, covering the details of his skills, how it got him assigned to one of the city's factions, and ended up becoming a lot more...personallyinvolved with the other factions.And then some other stuff, too.
Relationships: Castiel/Dean Winchester/Sam Winchester, Dean Winchester/Sam Winchester
Series: Angels and Demons Verse [17]
Series URL: https://archiveofourown.org/series/937254
Comments: 3
Kudos: 35





	Story Per a Life

**Author's Note:**

> I finished this last week but it wasn't until yesterday that I got the last scene done, and today that K beta'ed over this for me to point out some plot holes. She still hasn't gone over the revisions, and so it's not as smoothened out as I want, but whatever  
> And yes, there will be more to come...dunno when tho

Castiel had been the obedient kid in his family. Actually, he wasn’t the only one, but he was aware of his behavior, and how he looked to outsiders. But he always had been and will be fine with the way things had been.

Aware… yes, that could be a word best suited to describe him, Castiel preferred to think. He was aware that others saw his twin brother as far more normal in comparison when they were younger. Emmanuel Novak was everything Castiel wasn’t. Outgoing, social, a loyal member of almost all the clubs at school, hell, even the popular jock. Whereas Castiel had been more reserved, preferring to keep his nose perpetually buried in his books – or so he let everyone think. Truthfully, he may have been quiet (which didn’t necessarily translate to shyness), but because of that, he was the first one to realize the captain of the football team (not his brother, thankfully. Emmanuel was the halfback) was cheating on his girlfriend (the head of the cheerleading squad, of course) with the lanky art kid behind the bleachers before first bell would ring.

Don’t ask Castiel how he found out that particular bit of information, though.

But the fact remained, the Novak twins were different in pretty much every aspect, leaving Castiel feeling safe enough to say that they only ever shared three similarities: parents, physical characteristics, and their passion for church.

Which was why it came as a surprise, Castiel mused, when Emmanuel became interested in the spiritual and holistic healing methods shortly after his marriage to a wonderful woman named Daphne… and Castiel began working for the FBI.

Yes, everyone to grow up with the Novak twins, or watch them grow – such as and including their parents – were thoroughly dumbfounded, but blessedly just went along with things. And Castiel went on to climb the ranks and ace his various trainings. Emmanuel’s decision to become a hippie may have admittedly been a little jarring for Castiel – but only because his brother had decided to actively embrace the life. Castiel figured there always had been that one little weird perk about his brother’s personality – just as much as he knew a critical position was it for him.

And call it intuition, or not, but seeing as it did lead Castiel to this specific section of training repeatedly…

“Time.”

Castiel stood back, spine straight and hands folded behind his back. He may have been staring straight ahead, but he didn’t miss Meg’s impressed look at the timer from where she was standing off to his side. 

“Two minutes, fifty-four seconds. Well, color me surprised if you haven’t just broken some sort of world record, Clarence.”

Castiel rolled his eyes, letting his posture loosen as he brought his hands to his sides. “I highly doubt that.” He moved onto the next table, more scattered equipment looking back at him. This time, however, he was supposed to assemble the explosive, and Castiel knew the device was as different as it could get from the one he had just – safely – taken apart.

“Sure,” Meg said. And then, voice sharper, “Go.”

Castiel’s hands positively  _ flew  _ as he assembled the explosive, eyes focused. The world around him faded from view, narrowed down to only what was in front of him. Swiftly, yet perpetually careful, he connected wires from one motherboard to another, occasionally looping something – really, just for himself – all under Meg’s watchful stare. His brain was blissfully blank except for mentally narrating his actions. He’d just connected one final wire when one of the tiny LED lights at the top of the board lit up. Castiel immediately stepped back, hands folded behind him – “Time.”

“Three minutes and forty-six seconds. Mm, Castiel, do you have somewhere to be?”

Castiel frowned. “No… why?”

Meg grinned, and he was wise enough to not comment aloud about how reminiscent of a predatory shark the expression looked on her. Knowing his friend as well as he did, though, Castiel figured Meg would only see the comparison as a compliment.

“Then let’s blow this shit up!” Before Castiel could respond, Meg was swooping up the little device he’d created. Flipping a small switch on the board, she swung back her arm – and then threw it  _ hard  _ at the training field.

Three seconds later, still mid-flight, the device exploded, littering the surrounding area with shrapnel.

Meg made an excited sound at the back of her throat. “My, my, Clarence. You really know how to get a girl revving, don’t you?”

Castiel gave her a hard stare, even as he perused her words in his head. “Was that… a pun?”

oOo

“Ah, Cassie!” Castiel cast a disdainful look at the man sidling up to him, easily matching his pace. There was no way the Frenchman’s attire was appropriate for a workplace environment. He looked more like a fashion designer with his outrageously skinny jeans – if Castiel didn’t know better, he’d say the fabric was painted onto his legs – and a t-shirt with a v-neck so low it possibly came down between his nipples.“Any idea what a new superior could possibly want with, well, you and me together?”

“Right here, asshole,” Meg snarked from Castiel’s other side. Balthazar Roché cast her an apologetic smile, waving his hand with a grand flourish as he bowed, before looking back at Castiel. 

“I haven’t the faintest idea, but I’m sure we’ll soon find out,” he stated neutrally. Balthazar looked at him speculatively as they turned into the hallway leading to the conference rooms. He didn’t say anything, although he gave Meg space instead to wheel herself ahead of them and, subsequently, take the lead.

Castiel held the door open for the other two to enter their room first before following behind. His eyes were keen to take in the essentially empty room – empty, except for the soul figure seated at the head of the table, feet propped up on it, and a lollipop stick sticking out from under the fedora hat covering the man’s face.

When Meg and Balthazar both refused to say anything first, blatantly staring at Castiel, if anything, he sighed, rolling his eyes and taking a step forward. He just opened his mouth when, in one fluid motion, the man uncrossed his legs and stood, easily slipping the hat in place atop his head.

“Good afternoon, fellas,” Mr. Gabe Jr. (none of them knew if that was all to the man’s name or not) stood proud and rg for all his previously lounging position. And with the lollipop still in his mouth. Yet, not a wrinkle creased his suit, nor was a hair out of place on the man.

Their new chief officer’s eyes glinted a dangerous gold as the setting sun cast its rays through the open window.

“I have work for you.”

oOo

“H-hi,” Castiel said, feeling Plastered and otherwise like a complete idiot. He was sure it showed too, as he winced and practically threw and started juggling with the papers in his hands. They were technically supposed to be in the file tucked under his armpit, but – “Oh my God, I'm terribly sorry.” He muffled a groan as he bent down to pick up the following papers, only to pause when a pair of sensible shoes stopped beside him.

Castiel, embarrassed, averted his eyes even as a redhead kindly helped collect his papers. “It’s totally fine!” The girl chirped. “Happens to all of us. I’m guessing you’re here for the job application?” They straightened, the girl handing Castiel his papers. This time, Castiel made sure to carefully tuck his resume into the file before hesitantly meeting the girl’s eyes.

“I-yes,” he mumbled. 

The girl beamed at him. “Cool! I’m Charlie, the person who looks after almost all the tech for the boss — which means I can get you in if I wanted to,” she winked at him as she rounded her desk, taking her place behind the computer.

Feeling a little off balance, yet emboldened somewhat at the wink anyway, Castiel leaned forward, putting an arm on the table — and noticed one of the photo frames. It was a picture of the redhead — Charlie, and another girl. Kissing. 

Castiel cleared his throat, but didn’t remove his arm. He did rethink his initial plan of leaning forward, though. “Uh, thank you? If you could get me in, that is — if everything’s right. I-I’m James Milton, and I should be meeting with-with a Mr. Megatron?”

Charlie found-and then her eyes widened. She snorted, clearly unbidden when she clapped her hands over her mouth. Castiel slowly started to tilt his head, making her look abashed as she reluctantly pulled her hands away. “Sorry. It’s just — I mean, you’d think I’d be used to it by now, considering how understandably common of a mistake it is,” Charlie tried to explain. “But it always catches me off-guard!”

Castiel began to frown. “I’m afraid I don’t follow,” he stated bluntly.

“Oh,” Charlie facepalmed. “It’s actually Meta _ tron _ . Not, like the transformer,” she gave him another sheepish smile.

“Right…” Castiel said slowly. Charlie continued to blithely smile. Castiel internally sighed. “So… Mr. Metatron?” He prompted.

Charlie abruptly straightened. “Oh, right! Of course,” she looked down at her screen, rapidly typing something on her computer. “Alright. Metatron will be down to see you in a moment. You’re welcome to sit down while you wait,” she gestured to the small lobby, but Castiel made no move towards it. Instead, he looked at Charlie, opening and closing his mouth like a brainless fish. Not failing to pick up on the sign this time, Charlie smiled sympathetically.

“Is there anything further I can help you with?” She asked kindly.

“Yes, actually… you mentioned — you said you’re good with tech?”

Charlie brightened, her face actually glowing at the mention. “Am I  _ good? _ Not to brag, but I think I’m an absolute BAMF.” She said confidently.

Castiel was just going to ask her what on earth a ‘BAMF’ meant when a voice popped up from behind him.

“Ah, you must be my eleven-thirty appointment.” Castiel turned today face the newcomer, but not before sharing a dubious look with Charlie.

“Mr. Metatron?”

The man — looked like a bullfrog, honestly — waved a flippant hang. “Just Metatron, no need for the ‘Mr.’ nonsense. I prefer to be on a first name basis with the staff, you understand?” He leered, even placing a hand on Castiel’s forearm. He stiffened, straightening into what Meg likes to call his ‘military-stance,’ attempting to covertly pull his arm free.

“Metatron,” Castiel acquiesced. “It’s, uh, half past one, sir.”

Metatron scrunched up his face. “I thought I said none of that title nonsense? Not with me!” He didn’t acknowledge his error with the time, Castiel noticed. “Follow me, please.”

Castiel glanced at Charlie. She shrugged, mouthing a, “Good luck!” Breathing deeply, Castiel let Metatron lead him to the elevators.

“So, James,” Metatron began, once they were in and headed to one of the floors near the very top of the building. “Based on what I’ve read from your application, I was suitably impressed to decide your skills could let us skip the whole, boring interview thing.” Metatron grinned. “Congratulations, boy. You’ve made it to the finals.” He said, rather ominously. Castiel’s frown grew ever deeper, the man’s greasy demeanor causing shivers to run up and down his spine not helping.

The elevator doors little open.

Castiel’s head sprung around to see none other than the head of the Angels’ faction standing right there, only a desk away. His fingers itched for a pair of handcuffs that weren’t there.

“ _ Not now.”  _ He told himself. “ _ Soon.” _

Metatron stepped out of the elevator. After a beat, Castiel followed, face schooled into a mask of polite indifference, with only a hint of nerves allowed to slip through for the façade of a man here for a job.

“Michael,” Metatron greeted. Michael looked up at the voice — and Castiel knew Michael didn’t actually do it, but it still seemed the man had been sorely tempted to roll his eyes. “Look at this fine specimen. Weren’t you complaining about the lack of a perfect, personal, muscleman? Well, James here —” Metatron continue to gush. Castiel didn’t fail to notice how he was just mindlessly listing out the skills he’d filled in his fake application.

Michael quickly turned his gaze to Castiel, scanning him from head to toe. His expression didn’t change. Castiel audibly swallowed, but kept looking straight ahead, having subconsciously retained his ‘military-stance’ again at some point..

Michael smirked. “He’s hired.”

Metatron came to an audibly stumbled halt. “C-Come again?”

Michael sighed, closing his eyes. Castiel recognized the expression all too well as one mentally requesting for patience. “He’s hired,” Michael said decisively. “Show him the ropes, talk payment with Adler, whatever needs to be done.” He waved a hand, returning to his book in the other hand. “You’re dismissed.” 

Metatron gaped, but recovered remarkably quickly. “Of course.” Castiel watched with hidden amusement as Metatron moved to enact an aborted bow before stumbling back to the elevators. He followed at a more leisure pace, and even more gracefully. As Metatron continued to natter on about the legalities or the like as soon as he punched the button for the elevators, Castiel paid him half an ear, but the entire time he was aware of a stare burning holes into the back of his neck.

Castiel and Metatron turned to face the entrance of the elevators once inside. Before the doors closed, he dared to risk a peek at Michael. Michael was studiously reading his little novel, casually sipping on a glass of wine.

oOo

Days turned into weeks turned into months before Castiel first laid eyes on the ever famous Dean Smith Winchester. He’d heard of him, or course — how could he not? There was the FBI’s abysmal report on the assassin, but embarrassingly enough, it was all formed from word on the streets, or whatever tidbits he’d managed to hear despite constantly hovering over Michael’s shoulder. Ultimately, the information they’d compiled of Dean S. Winchester only filled a little less than a page.

Recruiting Charlie Bradbury helped them add another line, before she claimed her computer frosted. Based on her expression when she’d recounted the tale made Castiel think she may have meant the phrase quite literally. 

Still. Castiel reread the report until he could see the words with his eyes closed. And yet, the vision of their first encounter continued to flash vividly behind his eyelids. 

He’d barely even spoken.

Vibrant green eyes roving over the photograph Michael had slammed on his table separating them. 

A husky voice accentuating a smirk.

“Consider it done.”

_ Dean Smith Winchester. Male. Possibly aged late 20s-early 30s. Family: unknown. Possible relation to John Winchester (see: file 90048C) Education: unknown. _

_ Occupation: former military. Tutored under ‘torture-extraordinaire’ Christopher “Alastair” Heyerdahl. Trained in hand-to-hand combat. Employs use of short-range weaponry, long-range weaponry, varying forms of blades and firearms. Proficient in martial arts. Witnesses claim the possibility of mixed styles in combat.  _

_ [MILITARY FORMS FALSIFIED. UNCLEAR INFORMATION] _

_ Currently freelancing as ‘hit man-for-hire.’ _

_ Multiple possible connections to Angels’ faction. Other gang involvement: unknown. _

Castiel didn’t doubt for a second that Dean Winchester was involved in way more than just taking out Michael’s unruly foreign opponents.

oOo

After Dean got out of the hospital — AMA, but Castiel was not getting in the middle of that conversation — Castiel couldn’t help but marvel at the oddity his life had seemingly become. On one, Charlie was furiously hacking database after database, trying to get as much technologically obtained information on Raphael as she could. With her help, Balthazar was forming a detailed layout, and — Castiel knew — all the possible ways they could enter and successfully take down Raphael in his own territory. 

Unfortunately, a private request for more information to be delivered from Dean’s hospital for his identity or even any other records proved for naught. They’d had nothing on him, as if Dean Winchester was a ghost that never existed and required their facilities at all.

On the other hand, Castiel was testing out the different kinds of weapons Meg had procured, and was examining them with none other than a well healed Dean himself. Sam — his  _ brother,  _ Castiel mentally gawked,  _ the leader of the demons’ faction and Dean Winchester were brothers  _ \- was busy talking to Frank Devereaux and Ash — his and Dean’s personal, off-the-grid techies — about something regarding satellites, if Castiel overheard correctly. He wasn’t too hung up on the details, knowing he’d be filled in soon enough. And sure enough, he was just set string to pick up one of the heavier guns — a Grenache launcher in layman’s terms, but one he and Meg had personally designed and created — when Sam approached them, face stony.

Even if he’d intended to question Sam, he was distracted by the widening of Dean’s eyes, making him look almost manic as he took in the easy way Castiel handled the heavy machinery. 

“Is that what I think it is?”

Castiel eyed Dean’s star-struck expression. “Quite possibly… yes?” Although, he wasn’t entirely sure, given Dean’s penchant for stealth considering the job he went around by. And the grenade launcher was anything but stealthy.

“Dude, yes.” Dean’s excited beam transformed his features into that of something more childlike. It was tempered, however, at Sam’s responding skepticism.

“Dude, nuh-uh.”

Feeling awkward, Castiel leaned back and zoned out as the brothers continued their banter. And that’s what it definitely was, some light-hearted teasing between siblings.

Except, Castiel had a brain that got him into the FBI with ease and efficiency for a reason. And it wasn’t because he ignored blatant signs that occurred right in front of his very eyes.

Like the clear fact that Sam and Dean weren’t just mock-arguing, but  _ flirting.  _ And they were standing far closer than necessary. 

Castiel looked away. Considering the things he knew, and the things he’d seen during his short but eventful life, he wasn’t going to judge. Didn’t mean he was going to openly and shamelessly stare, though.

“Obsessed as I am with you and your body,” Dean was saying. Heat flooded Castiel’s cheeks when he noticed what he’d tuned back into. He subtly tried to adjust his hold on the launcher — only to freeze when Dean let out a moan. “But you gotta admit,” Dean’s voice took on a breathy admiration, tone practically dropping an octave lower. “That is hot.”

Castiel, trained FBI agent, with multiple field cases under his belt — remarkable for a thirty-something year old (who was counting anyway) — jumped. He was pretty fairly certain that at that moment, he, Castiel Novak, was screwed, because  _ dear lord did Sam actually just growl at him? _

“Down, boy,” Dean pressed his hand to Sam’s heaving chest, but he was still looking at Castiel as well.

He wasn’t sure whose stare was worse: Dean’s lust filled one, or Sam’s eyes promising him a slow and painful death. 

“ _ Oh, yeah,”  _ Castiel’s mind decided to help fully provide. “ _ Totally just brothers.”  _ He resisted the urge to pull the launcher on himself, if only because he knew it would only cause more trouble than it was worth. Instead, he made a mental note to thank Meg later for teaching him how to emote better and flawlessly for donning another persona as needed on the field, but not to the point that he unwittingly experienced character bleed. 

His default poker face he’d pretty much been born and raised with was far too beneficial to replace. Especially in moments like this, where one particular Dean Winchester seemed invested in testing his pokerface’s durability. 

“Maybe we could rope him into one of our games?” Dean whispered suggestively to Sam, but Castiel could still hear him all too well. The hand that was pressed to Sammy’s chest was now moving up and down in a stroking gesture, but at least he’d redirected his sultry gaze from Castiel to Sam. 

The fires in Sam’s eyes tempered, only to take on a different quality.

oOo

_ “Now, Cas.” _

Castiel let the grenade launcher fall to his side, hearing alarm after alarm go off.

The building in front of him crumbled, burying Raphael’s men in its rubble. Castiel set down the grenade launcher, and started to dismantle his sniper gun. 

Two minutes later, he was jumping down the building he’d been stationed at, the wind whistling in his ears. His feet touched the ground, and with the click of a button, his rope was falling in a large heap at his feet. He abandoned it, running into the building on the other side of the crumbled remains he’d brought down, still disturbing the air with its dust. 

Castiel armed himself with a gun in each hand while on the move. His backpack bounced with every step he took. It didn’t bother him — not as much as the unnerving silence he was met with when he entered the building. It didn’t take Castiel long to find out the reason behind the unnaturally still air.

The lobby was littered with corpses. At first, Castiel attempted to look for survivors. It soon became clear that he wouldn’t be needing his handcuffs after all, though. 

The stairwell, in stark contrast, was jarringly empty. Castiel still refused to relax his stance throughout the entire climb to the building’s top most floor. A floor short of of the balcony, Castiel exited the stairwells, and came to a halt.

The wind whispered in his ears through the open windows, accompanying the soft cooing echoing itself at his feet. 

In the center stood Sam, expressionless as he stared down at the lone corpse at his feet. As Castiel continued to silently watch, Sam bent down, unheeding of the pigeons covering the entire ground save for the space the corpse took up, and the area where Sam stood. 

On Raphael’s unmoving chest, Sam places a dark red rose, the petals withered and about to fall off, the leaves near crumbling stage. 

Castiel took a step toward, entering into the room. Miraculously, he didn’t crush any pigeons under his feet, the birds swift to move away. Regardless, Sam’s head shot up. Still bent down and unmoving, he locked eyes with Castiel.

Castiel couldn’t breathe when he met Sam’s gaze, and saw what his eyes beheld within them. 

Sam slowly straightened. Castiel took another step forward — and the world colored into white as every single pigeon simultaneously took flight. Forced to freeze, Castiel stood, glaring at the whiteness, trying to see past it all. Too soon, however, the birds were settled, as abrupt as they’d startled, now looking to be at utter ease. 

Sam was nowhere to be seen. By the time the coroners arrived an hour later at the crime scene, the rose on Raphael’s chest had been ridden of all its petals, giving way to time. 

oOo

Castiel groaned, pulling his arms. It was a useless maneuver, considering they were handcuffed above his head.

Castiel wouldn’t say he was one for pride… but he was pleased whenever anyone commented on his usually stoic appearance. The rapid reddening encircling his wrists, however, was fighting hard to prove anyone who’d ever said so wrong.

Dean hummed, the muffled sound still coming across as clearly amused. With a grunted gasp, Castiel glared downwards where Dean was currently between his legs. If Dean’s hands weren’t doing their best to keep Castiel’s legs apart, he would have closed them to momentarily suffocate Dean. Not that he would relish in the sadistic action, unless it was something they’d talked about.

Considering Sam’s watchful eyes from behind Dean, though, Castiel knew he was lucky to even be where he was.

Letting his eyes close and head fall back again, Castiel focused on sensation alone and ignored his other senses. Well. Except for his hearing. Because the lewd and filthy sounds of Sam slamming into Dean’s well lubed hole, the sound of flesh hitting heated flesh, was too good to dismiss. It was the sound of dreams, combined with Dean’s lustful moans muffled around Castiel’s dick, a soundtrack that Castiel ensured would be forever embedded in his spankbank in the future. 

And the sensations… _ heavens above _ , Castiel could safely say that never before had a man or woman gone down on him with such exquisite skill before. The way Dean’s tongue artfully licked around his head every time he pulled off and before ducking back down, the way Dean’s throat flexed, tickling at the head of Castiel’s cock where it hit the back of it, never before had Castiel had been brought to this extreme level of arousal from the devout attention focused on his dick alone. He would’ve come several times by now, too, if it weren’t for the cock ring locked around the base of his dick.

Castiel groaned louder as Dean chose that moment to wrap a hand around his balls and tug, toeing the line between pain and pleasure. And that was another thing – apparently, Castiel had a pain kink when he was the submissive. Or maybe it was just the brothers… 

Sam huffed, the sound bringing Castiel to open his eyes and witness how he bent his head, letting his long hair fall over and cover his face as he was brought closer and closer to his orgasm. Out of the three of them, he was the only one to not wear a cockring, but Castiel figured it had more to do with Sam simply not needing it. They’d been going at it for what must’ve been  _ hours _ now, and Sam had yet to come, even as Castiel and Dean’s cocks grew darker in color from their denied orgasms.

Dean keened as Sam hunched over, folding himself along the length of Dean’s back and eliminating any space between them. As Castiel watched, Sam whispered into Dean’s ear, pressing teasing kisses to his earlobe between every alternative thrust, licking and nibbling between every third. Castiel couldn’t hear what was being said, but it clearly must’ve been something fairly erotic, as Dean’s mouth went absolutely slack around him, eyes rolling to the top of his head before Dean’s eyes closed, hiding his mesmerizing green orbs from view. Sam brought a hand up from Dean’s hips, and still whispering something into Dean’s ear – his lips hidden by flesh and rendering Castiel unable to read what he was saying – he looked up, his dark gaze finding Castiel. Sam grinned a slow, evil smile.

Castiel shouted. Sam’s hand had covered Dean’s on Castiel’s balls, and were yanking and twisting in ways Castiel never would have dared to do to himself. But under Sam’s – and Dean’s, if lax – hands, it was perfect, agonizing pleasure. Castiel bucked his hips, growing more desperate by the second to reach completion, but still held back. It was only after Dean gagged that he realized what he had done, but the fog of lust was too heavy for Castiel to do more than cast a cursory glance at Sam. Thankfully, Sam only seemed amused rather than angered.

And then Sam’s face was scrunching up, and he hid his face in Dean’s neck. His thrusts grew more frantic, hitting hard and deep, rocking Dean up the bed and pushing him further down Castiel’s cock in the process. Castiel squeezed his eyes shut – and then wrenched them open with force. There was no way he was going to miss out watching this once in a lifetime opportunity play out to the full. 

It was with a yell, that Sam came, muffled as he bit into Dean’s shoulder. Dean whined, loud and unrestrained in return, pulling off of Castiel’s cock to let the sound echo through the room. Sam’s hips worked through his orgasm, and Castiel could only imagine Dean’s ass flexing, squeezing, wringing Sam’s come out of him and deep within his older brother. The cold air abruptly hitting his cock had Castiel hissing, tears actually springing to his eyes, and he pressed his head hard against the pillow, chest heaving though it was Sam who was slowly coming down from his orgasm.

Dean moaned, falling, limp, to let his head rest against the crook of Castiel’s thigh, tiredly nuzzling his twitching cock.

Sam pulled out. For all that he’d just blown his load pretty hard, he looked too energetic for a man who would by all means be ready to collapse. With swift movements, he was flipping Dean onto his back and lifting him higher, until he fell beside Castiel on the bed. Castiel watched, helpless and unable to move, as Sam pushed his still sizeable cock back into Dean. Dean’s back arched, and he hadn’t even reached the zenith of his curve before Sam was yanking off his cock ring. Ramming his hips to the point that Castiel felt tempted to wince in sympathy, Sam jerked Dean off with harsh strokes, sharp eyes never leaving Dean.

Dean, who had his own eyes still closed, whimpered, high pitched moans and keens that sounded like honey to Castiel’s ears. Turning his head blindly to the side, he reached out. Castiel cast a hesitant glance at Sam, but with no reprimands seemingly coming, Castiel leaned forward, and met Dean’s lips in a soft kiss. It was more a press of mouths, really, Dean too far gone to do anything more than breathe, his mouth slack, into Castiel’s mouth. He didn’t care much, however, taking advantage of the moment to nip at Dean’s luscious lips, licking into Dean’s mouth.

The sound Dean made when he came?  _ Glorious. _

Dean was left panting on the bed, loose-limbed and already looking like he was well on his way into la-la land, when Sam turned on him. Castiel eyed warily, but Sam reached above, and unlocked the handcuffs. Castiel brought his hands down, rubbing at his stinging wrists, when Sam surprised him by taking Castiel’s hands in a hold far gentler than he’d have expected, coming from Sam. Pressing a kiss to the angry red mark on each wrist, Sam pushed his hands back onto the pillow besides Castiel’s head. Castiel watched, never taking his eyes off as Sam straddled him, sitting up tall and mighty, and then ground down on Castiel’s dick.

Castiel closed his eyes, breath catching. One of Sam’s hands let go, disappearing before reappearing at Castiel’s throat. Still, he kept his eyes closed as Sam squeezed. Sam circled his hips, Castiel bucking up for more friction, his head growing lightheaded.

Sam abruptly let go, and Castiel gasped for breath, eyes shooting open. Black spots danced in his vision, and still, he moved his hips to meet with Sam’s accordingly, an unexpected dance nonetheless all too welcome. His balls may have felt like they were about to burst, but when Sam started to squeeze again, Castiel bared his neck. He growled when Sam pulled away instead, eliciting a dark chuckle, and then he was squeezing again, harder.

Castiel cried out, thrashing. His feet pressed into the bed, trying to press up, aching for friction.

Dean continued to doze, blissfully unaware, right beside them, although a small smile was playing on his lips. 

Just when Castiel was sure he was about to pass out, Sam let go. He heaved, arching and gasping for breath – Sam pulled off his cock ring, and Castiel came with a hoarse yell, the world around him blacking out.

**Author's Note:**

> If you haven't guessed already, the big climax/final showdown whatever will not be told in one go, but rather in bits and pieces from Dean (done) Cas (done) and Sam... which might actually cover the brunt of it considering its his series, apparently. Yeah, ik, its a risky maneuver, and I'm nowhere near talented to pull it off/execute it as well as it should/could be done, but, welp? I'm hoping for the best anyway cuz I'm too lazy and tired to sit down and do the scene in one go. might end up taking too long and being too long for that
> 
> ALSO, please comment!! I need to know what y'all think or want or whatever – your comments feed me motivation to help me get the next pieces out sooner!!!!!!


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